USPTO Patents Application 09937762

©

J)

Europaiscries Patentamt
European Patent Office
Office europeen des brevets

© Publication number:

0 375 624

A1

©

EUROPEAN PATENT APPLICATION

© Application number: 89810966.5
© Date of filing: 19.12.89

© int. Ci. s A01N 25/18, A01N 33/02,
A01N 33/04, A01N 33/08,
A01N 43/84

© Priority: 23.12.88 US 289165

Applicant: sandua, a<j

Licntstrasse oo

© Date of publication of application:

CH-4002 Basei(Un)

~ 27.06.90 Bulletin .90/26 . .

ac /^lj cc cd fie* rtP it i till Ml *>P
Be wn to rn vjd Van II^UJ LU r*i~ oc

© Designated Contracting States:

Applicant; SANDOZ-PATENT-GMBH

AT BE CH DE ES rn Go Gn IT LI LU NL oc

nuiiiuuiuiwii qoqc w

D-7850 Lorrach(DE)

©

DE

Applicant: SANDOZ-ERFINDUNGEN

Verwaltungsgesellschaft m.b.H.

Brunner Strasse 59

A-1235 Wien(AT)

©

AT

©

Inventor: Burns, Johnny Lee

1 1246 South Green Street

Chicago III. 60643(US)

Inventor: Wilson, Richard Hansel

6014 Parkland Drive

Corpus Christ! Texas 7841 3(US)

© Low volatility salts.

© Pesticidaily active compounds in amine salt form have reduced volatility compared with the free-acid form
and other salt forms.

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Xerox Copy Centre

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EP.O 375 624 A1

LOW VOLATILITY SALTS

; This invention relates to the ' use of'. various salts 'to reduce the volatility of biologically active
compounds. More specifically, this invention relates to pesticidaily active compounds in particular salt
forms, the same;having reduced volatility as compared with the free-acid form and other salt forms;

It has been found in accordance with this invention' that certain amines are particularly useful- in varying
amounts in reducing the volatility of pesticidaily active compounds, i,e. herbicidally, insecticidally, and
fungicidaily active compounds, which bear a carboxylic acid group, and may even be used for- such
purpose upon simple addition to other salt forms.
Pesticides; which~exhibiHow7^

only be damaging to sensitive. off-target pests, but may be less effective on target pests.

■It has been found that amines, selected from the group consisting of
.. _a)..Aminopropylmorpholine-(APM) as-shown.by-the formula-! — — -— — ■ - ■ . ■ ..- ■ ■

•" CH 2 -CH 2

v - : v . '•■ . / .

. 0 ^N-CH 2 -Cff 2 -CH2-NH 2 . I;

CH 2 -CH 2

b) Jeffamine D-230 as shown by the formula II ..

H 2 N-(j;H-CH2-<0^CH 2 -CH-) n NH 2 II

■ CH 3 ;■• ';. CH 3 ..

wherein n is 2 or 3;

c) Methyldiethanoiamine : (MDEA) as shown by the formula III
CH3-N-(CH2-CH 2 -OH) 2 -- III;

d) 2-amino-2-ethyl-l I 3-propanedioi (AEPD) as shown By the formula IV

' CH 2 -OH
I

H 2 N-C-CH 2 -CH 3 ' ■ IV;
CH 2 -OH-

e) Tris(hydroxymethyi)aminomethane (Tris Amino) as shown by the formula V

CH 2 -OH.

i •
H 2 N-C-CHa-OH V; and

CH 2 -OH

O^^.S-TrisfdimethylaminomethyOphenol .(Actiron NX-3) and NaOH as shown by the formula VI

- OH

(CH 3 )2N-CH 2 ^^^ca 2 -N(CH 3 ) 2 + NaOH VI;

; CH 3 -N(CH 3 ) 2 .

substantially , reduce the volatility of pesticidaily active compounds without adversely affecting their-
pesticidal. activity. Thus one aspect of this invention is to provide pesticidaily active compounds in the

EP 0 375 624 A1

aforementioned amine sait form, and mixtures thereof.

The preferred classes of -herbicidal compounds whose volatility is reduced in accordance with- this
invention are the carboxylic acid- containing compounds which include glyphosate. the benzoic acid
compounds! the phenoxy carboxylic acid compounds, and mixtures thereof. Particularly preferred com-
5 pounds include MCPA (2-methyl-4-chlorophenoxyacetic acid), dicamba (3,6-dichloro-2-methoxy-benzoic
acid), and I 2,4-6 (2.4-dichlorophenoxyacetic acid). A particularly preferred embodiment are the APM salts of
. dicamba and 2,4-0, and mixtures thereof. Another herbicidal carboxylic acid of particular interest is'
glyphosate (phosphone-methyi glycine). ■■.
Specific fungicides which may be mentioned for conversion to amine salt form include Curitan (N-
w dodecyl guanidine acetate) and Miiban R (dodemorph acetate).

The amine salts of this invention may be made by combining any of the aforementioned- amines of
Formulae I to VI with a pesticidally active compound, i.e. a. herbicidally. insecticidally or fungicidal^ active
compound either neatly or with the compound in its available formulation, for example,- dry or solid
formulations as. well as liquid formulations such as aqueous formulations. Also,. the amines of Formula I to
75' VI may be added to the pesticidally active compound which is already in another, salt form. Such
preparations are preferably carried out in aqueous media. For example, an amine of Formula I to VI may be
added to dicamba in dimethyiamine (DMA) salt form (commercially available from Sandoz Crop Protection
Corporation under the trademark BANVEl R ) in an aqueous solution at any suitable temperature; e.g., room
temperature. .In .a like manner, the amine of Formula I to VI and a different salt-forming base may be
20, combined with the free acid form of the pesticide "iri either case; it is indicated that minor amounts- of the
amine of Formula I to VI are effective to. reduce the volatility of the pesticide in the obtained mixture. Such
combination may be used advantageously to reduce the amount or a more expensive amine of Formula I to
VI while maintaining greater total salt formulation and low volatility.

The amount of added amine of Formula I to VI may vary widely up .to the amount required to neutralize
- 25 the acid or may be in excess of that amount.' The amount of the amine of Formula I to VI may be
designated with reference to "the amount of that amine required to bring a simple aqueous solution of the
■ pesticide to a pB of 8. For example, if a composition is "1.5X", then it contains 1.5 times the amount of the
amine of Formula I to VI necessary to raise the pB to 8. Preferred compositions according to this invention
generally contain at feast 0. 1X, and are preferably in the range of 0.1 to 3X the amount of the compound of
"30 ' Formula I- to V, more preferably 0.5 to 2:5X and most preferably 0.5 Xo 1.5X the amount of the amine of
Formula.! "to VI required.

the pesticides of this invention may be applied and used as'pesticides in the same manner and at
essentially the same dosages as the parent compounds prior to combination with an amine of Formula I to
VI have been used. Somewhat lower dosages'^ may be used in cases where volatility has increased the

35 actual effectiveness of the compound; -

' The invention is of particular interest for use. with compounds effective at combatting weeds, such as
dicamba/ 2,4-6, or mixtures thereof - by .applying the amine salt form of this invention in a herbicidally
effective amount to the weed plants or their locus. ■

Generally the amine salts of this invention will be applied at' rates depending upon recognized factors

40. - such as the specific amine salt, the plants primarily in the locus, the timing, mode and formulation in
application, the various conditions of treatment such as soil and weather and the like. However, in general,
satisfactory results in weed control are usually obtained upon application of the amine salts of the invention
"at a rate in the range of from 0.05 to 10 kg/hectare, more usually 0.05 to 2 kg/hectare, and preferably 0.1 to
1 kg/hectare., the application being repeated as necessary. When used in crops, the application usually will

45 not exceed about 5 kg/hectare, and is usually in the range of 0.1 to 2' kg/hectare.

Another aspect of this invention relates to compositions comprising the amine salt of a pesticidally
active compound, wherein the amine is selected from the, group consisting of the amines of the Formula I to
VI as previously defined in combination with an agriculturally inert carrier, either in concentrate form or in
dilute form for agricultural application. Concentrates may be in solid form with conventional inert solid

50 carriers and optionally other conventional adjuvants such as wetting agents, sticking agents and the like.
Preferably, the compositions are in liquid form and more preferably comprise water as the inert carrier in an
amount at least sufficient to dissolve the pesticides of this invention and other salt or free acid form of the
compounds present, and excess amines of Formula I to VI .which may have been employed, and optionally
adjuvants such as wetting agents and the like. Such compositions may also include other pesticides.

55 Such compositions may contain 0,01% to 99% by weight of the pesticides of this invention, from 0 to
20% by weight of agriculturally acceptable surfactants and 1 to 99.99% by weight of the inert carrier.
Higher ratios of surfactant to active ingredient are sometimes desirable and are achieved by incorporation
into the formulation or by tank mixing. Application forms of composition typically contain between 0.01 and

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EP 0 375 624 A1

25% : by , weight of the pesticides of this invention, but lower or higher levels can, of course, be present
depending on the intended use and , the physical properties of the pesticide. Concentrate forms of
/composition .intended to be diluted before use generally contain between 2 and 90%, preferably between 10
and 80% by weight of active ingredient.
5. Useful compositions or formulations of the compounds of the invention -include dusts, granules, pellets,
suspension concentrates,. wettable powders, emuisifiable concentrates and the like. They areobtained by
conventional manner, e.g. by mixing the pesticides of the invention with the inert carrier. More specifically,
liquid compositions are obtained by mixing the. ingredients, fine solid compositions by blending and, usually
grinding, - suspensions by. wet milling and granules and pellets by impregnating or coating (preformed)
: w ■ granular carriers with the pesticides or by agglomeration techniques.

For example, dusts can be .prepared by grinding and blending the pesticide with a . solid inert carrier
^"such^as-talci^cia^

, usually, dissolved; in a suitable solvent, onto and into granulated carriers such as the attapulgites or the
* . verm.iculites, usually of a particle .size range of from about 0.3* to 1.5 mm. Wettable powders, which' can be
^5— dispersed-in-water-or-qi^ prepared ~rjy"i ncorporat ing"
- wetting agents into concentrated dust compositions...;

Alternatively, the pesticides of this invention may be. used in : micro-encapsulated forrnv*- - ■
Agriculturally acceptable additives may be employed in the compositions to improve the performance of
the pesticide . and to reduce foaming, caking and corrosion. ■ '.' ■

-20-... ■ Surfactant as used herein means agriculturally acceptable material which imparts emulsifiability,
. spreading, wetting, dispersiblity or other surface-modifying properties properties. Examples of surfactants
v are sodium lignin. suiphonate and., lauryl .sulphate. '

- Carriers as used herein mean a liquid or . solid material used to dilute "a concentrated material to a
•usable or. desirable strength. For dusts or granules it can be e.g. talc, 5 kao!in or diatomaeous earth, for liquid
25 concentrate forms, a hydrocarbon such .as xylene or an alcohol such as. isopropanol; and for liquid
application forms, e.g. water or diesel oil.

The compositions. of this application can also comprise other compounds having biological activity, e.g.
■ compounds having similar or complementary activity or compounds having antidotal, herbicida! fungicidal or
\ ihsecticidai activity. ' ... • '* \

30 :■. Typical pesticidal composition, according .to this invention, are illustrated by the following Examples A,
B and C in which the quantities' are in parts by weight. '

EXAMPLE A

35

Preparation of a Dust

-.- 10 Parts of an amine salt according . to this 'invention and 90 parts of powdered talc are mixed in a
.mechanical grinder-blender and are ground until a homogeneous, free-flowing -dust of the desired, particle
. . size is obtained. This dust is suitable for direct application to the site of the weed infestation.

EXAMPLE B

45

Preparation of Wettable Powder

- 25 Parts of an amine salt according to this invention are mixed and milled with 25 parts of synthetic fine
silica, 2 parts of sodium lauryl sulphate. 3 parts of sodium ligninsulphonate and 45 parts of finely divided
kaolin until the mean particle size is about 5 micron. The resulting wettable powder is diluted with water
before use to a spray liquor with, the desired concentration.

55 "* EXAMPLE C

Preparation of Emuisifiable Concentrate (EC)

•. ' . • ■ . . • 4

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EP 0 375.624 A1

13.37 Parts of an amine salt. according to this, invention are mixed in a. beaker with, 1.43 parts of Toximui
360A (a mixture of anionic and non-ionic surfactants containing largely anionic surfctants), 5.61 parts of
Toximui 360A (a mixture of anionic and non-ionic surfactants containing largely non-ionic surfactants), 23.79
parts of dimethyiformamide and 55.8 parts of Tenneco 500-100 (predominantly a mixture of alkylated
5 aromatics such as xylene and ethylbenzene) until solution is effected. The resulting EC is diluted with water
for use.

The invention may be better illustrated by reference to the following non-limiting examples. Throughout;
the examples, the term BANVEL R refers to dicamba-OMA. ■

10 : - '

EXAMPLE 1

15 Compositions

A formulation of each compound is prepared by suspending a* known quantity of dicamba and/or 2,4-D
in a known quantity of distilled water: This is titrated with the base to a minimum pH of 8.0, recording to.,
amount-of base added.: Additional water is then added to adjust to the appropriate concentration of active
20 ingredient desired. Typical formulations are given below. ' _ " '" .*'" ~ """ ™ J " " . *" '""

30,

1. 2,4-0 - DMA 439 g/t or 3.7

lb/gal ■

w/w %

2,4D tech (95% ae)

41.66

DMA (60%)

14.45

Distilled water

43.89

100.00

II. Dicamba - DMA 480 g/l or 4.0 .

35 _ ■ f

• lb/gal

w/w%

Dicamba Tech (80%)

■50.00

DMA (60%)

17.00

40

• Distilled water

33.00

100.00

45

Ilia. Dicamba - Tris Amino 480 g/l

w/w%

Dicamba Tech (90.7%)

41.19

Tris Amino

28.05

Distilled water

30.76

100.00

55

5

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EP 0 375 624 A1

lllb". 2,4-0 Tris Amino

. w/w% * '

2,4-0.(100%)

25.00

Tris Amino.

13.70

Distilled water

61.30

100.00

• 20

lllc. Dicamba- 2,4-1
Amino

D - Tris

•w/w%

2,4-D.(100%)
Dicamba (100%) '
Tris Amino
Distilled water

12.50 .
12.50
13.70
41.95
,100,00

Hid. Dicamba- 2,4-0 - DMA .

- Tris Amino '

w/w%

2,4-0 (100%)

12.50

Dicamba (100%)*"

- 12,50

DMA

5.09

Tris Amino

13.07

Distilled water ■

56.21

100.00

40 '

IVa. Dicamba - Jeffamine 0-230. ■

w/w%

Dicamba tech (90.7%)

43.79

Jeffamine D-230

24.28.

Distilled water

- 3 1.93 :

100.00

55 -

IVb. 2.4-0 - Jeffamine

w/w%

2,4-0 (100%)
Jeffamine D : 230
Distilled water

25.00
24.77
50.23
100.00

6

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EP 0 375 624 A1

IVc. Dicamba - 2,4-D - '

Jeffamine

w/w%

Dicamba (100%)

12.50

2\A-D (100%)

12.50

Jeffamine D-230

24.77.

Distilled water

50.23

100.00

IVd. Dicamba - 2,4-D -

DMA - Jeffamine

w/w%

20

Dicamba (100%)

12.50

2,4-D-(.100%)

12.50

DMA (100%)

5.09

Jeffamine D-230

. 24.77

Distilled water

45.24

25

100.00

Va. Dicamba - AEPD

w/w%

Dicamba tech (90.7%) .

42.85

AEPD

'29.09'

Distilled Water

28.06

100.00

. ^5

Vb. 2,4-D AEPD

w/w%

2,4-D (100%)

25.00

AEPD

13.48

Distilled water

61.52

100.00

- 50

7

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EP 0 375 624 A1

Vc. Dicamba - 2,4-D AEPD

w/w%

Dicamba (100%).

12.50

2,4-D (100%)

12.50-"

AEPD

* 13:48

Distilled .water

61.52 .

100.00

Vd. Dicamba - 2,4-D - DMA'

- AEPD

w/w% ;

Dicamba (100%).

12.50

2,4-D (100%)

12.50

DMA (100%)

. 5.09

AEPD

13.48

Distilled water

56.43

100.00

.25

30

Via. Dicamba - Actiron NX-3

w/w%

Dicamba (tech) (89.6%)

33.87

Actiron NX-3

7.67

; NaOH (50%)

7.87

Distilled Water

50.65 .

:100.00

40

45 '

Vlb. 2,4-D - Actiron NX-3

w/w%

2,4-D (100%)

, ,25.00

Actiron NX-3

7,78

NaOH .(50%)

4.52

Distilled water

62.70 •

100.00

50

55

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EP 0 375 624 A1

w

Vic. Dicamba - 2,4-D

Actiron ina'o

w/w%

Dicamba (100%)

12.50

2*4-0 (100%)

12.50

Actiron NK-3

7.78

NaOH (50%)

4.52

Distilled water

62.70

100.00

Vld. Dicamba - 2,4-D -

. DMA - Actiron NX-3 .

w/w%

■ Dicamba(100%)

,12.50

2,4-D (100%)

12.50

: DMA

5.09

Actiron NX-3

1 5.56

Distilled water

54.35

100.00

Vila. Dicamba - MDEA " . *.

w/w%

Dicamba Tech (89.6%)

23.97

- MDEA

14.41

Distilled water

. 61.62

100.00

40 ■

45

Vllb. 2.4-D - MDEA

w/w%

2,4-D (100%)

25.00

MDEA

13.48

Distilled water

61.52

100.00

55

9

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EP 0 375 624 A1

Vile. Dicamba - 2,4-D -

MQEA —

w/w%

• Dicamba (100%)

. 12.50

2,4-D (100%) '

12.50

MDEA -

13.48

Distilled water

61.52

100.00

— Vlld,-Dteamba — 2 7 4-D — — —
. DMA - MDEA

w/w%

Djcamba (100%)
2,4-D (100%)
DMA
MDEA

Distilleded water .

12.50
12.50
5.09
13.48
56.43
100.00

25 '

Villa. 2,4-D-APM 230 g/i or

1 .9 ib/gal .

w/w%

2,4-0 Tech (95%)

21 .82

. APM

19.41

Distilled water

58.77

100.00

Vlllb. Dicamba-APM 480 g/l or 4
Ib/gal '

w/w%

Dicamba Tech (90.7%)
APM

. Distilled water

43.42
.14.17
42.41
100.00

50

55 ■

10

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EP 0 375 624 A1

V

.5

VIllc. Dicamba-APM 196 g/l or
1 .63 lb/gal

w/w%

Dicamba Tech (90.7%)
APM . t
Distilled water

/ 19.67
* 18.64
61.69
100.00

70

15

Vllld. Dicamba + 2.4-D-APM

(1:1 ratio) APM

Dicamba 120 g/l or 1 lb/gal

2,4-D 120 g/l or 1 lb/gal

w/w%

Dicamba Tech (88%)

11.70

2,4-D Tech (95%)

10.88

APM*

20.16

Distilled water

57.29

100.00

Vllle. Dicamba + 2,4-D-APM

(1 :2 ratio) APM • /

Dicamba 55.2 g/l or 0.46 lb/gar-

2,4-D 1 1 0.4 g/l or 0,92 lb/gal

w/w%

Dicamba Tech (88%)

5.84

2,4-D Tech (95%)

10.85

APM

15.12

Distilled water

68.19

100.00

45

Vlllf. BANVEL R herbicide
+ APM

Dicamba 440 g/l or 3.67
lb/gal

50

w/w%

55

Dicamba (83%)
DMA (100%)
APM

Distilled water

42.63
10.61
11.55
35.21
100.00

11

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EP 0 375 624 A1

Vtllg. BANVEL* herbicide
' + APM

5

Dicamba 333 g/l or 2.8
lb/gal

w/w%

10 '

Dicamba (83%) •
DMA (100%)
APM

Distilled water

34.63
8.62
28.16
28.59

-100:00-

75 , ■ ~ ■ , -- - —

• EXAMPLE 2

.20

25

30

Volatility Studies' ' ■ ,

Compositions* from Example 1 are tested for volatility reduction and compared* to 'technical dicamba.
Each of the values below isthe estimated half-life based on CI* measured loss from a petri plate.

" Salt formulation of -

Half Life

Fold Reduction

Dicamba

(hrs)

in Volatility

Technical Dicamba

- 36

Tris Amine .

4101 .

114

AEPD

6277

174

MDEA

' 6111

• 170 .

Actiron NX-3

no volatility measured

35

40-

EXAMPLE 3

45

■50

55

Field Studies of Volatility

In this Example and the examples that follow, plot sizes-are calculated from meausurements originally
made in acres and lbs. according to the conversion factors: 1 hectare 2.47 acres; 1 kg = 2.2 lbs; 1 m =
3.28 ft; 1 psi = 0.07 kg/sg.cm; 1 gallon = 3.78 1.

Herbicide volatility is measured in a common Bermuda grass pasture with a plot size of 0.04 ha.
Application of herbicide is made at a rate of 0.45 kg active ingredient per acre with a C02-powered back-
pack sprayer and 3.7 m boom containing eight- equally spaced 8004 flat-fan spray nozzles at 2.0 kg/sg.cm
pressure and 243 liters of water per ha.

Three Gilian model HFO-113A air sample pumps are placed equal distance downwind to the center of
the plots,* 3 minutes ..after completion of the spray application, for a period of 8 hours. Air samples are
collected -at a rate of 2.6 liters per minute into plastic cassettes containing SKC-227-7 filter pads and are
analyzed for herbicide levels using standard , gas chromatographic procedures and a Hall detector. The limit
of detection is 0.01 ug/sample, and results presented are the average of three measurements.

The studies, are performed on days when no rain fell. Temperature was 88* F, and relative humidity
68%. Results are presented below. .

12

BN8DOCID: <EP 0375624A1_U»

EP 0 375 624 At

Salt of

- rOlu

dicamba

reduction"

Tris amine

17X..

AEDP

13X .

Jeffamine

1 2X ■ ■ '

Actiron NX-3

6X

10

'Reduction is compared with.Banvel Herbicide. All salts in this
study are titrated to pH 8.0.

.75

EXAMPLE 4'

20

The protocol described in Example 3 is followed to field-test the 2,4-0 formulations and dicamba-2 t 4-D
formulations, with the exception that plot sizes vary from 0.04-0.4 ha and application rates vary from 1.1-2.2
kg active~ihgredient per ha. Temperatures range from- 75-91 V F and relative -humidity from 48-74 % -Results
are presented below.

25

30

35

Herbicide

Rate (kg active

Volatility

ingred. per ha)

.{ug>-

2,4-0 - DMA

2.2

0!29

2,4-6 : - APM '

2.2

0.01

dicamba - 1.5X DMA

1.1

1.13

dicamba - 1.5X APM

1.1

0.024

BANVEL R

1.1

1.10

BANVEL R + 0.5X APM

1:1

0.08

. BANVEL R + 1.4X APM

'1.1

0.03

EXAMPLE 5

4Q

45

Effect of Addition of APM to 2,4-D and Dicamba Mixtures.

The following formulations are evaluated using conditions as described in Example 4. Results presented

below are the averages of three tests.

50

55

13

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EP 0 375 624 A1

Volatility (u.g)

neruiciue

Rate*

Dicamba

2,4D

Volatility reduction '

, Volatility reduction

compareu to

; Dicamba-DMA

2.4D-DMA

BANVEL*

.. 1-1

1.1

1.5X APM-dicamba

i .1 ■

0.024

46X ,

2,4-D (DMA) , '

. 2.2

0.293

1.4X APM-dicamba + 2,4-0

1.1 +1.1

■ 0.01

0.003

, 11 OX -

97X

1.4X APM-dicamba + . 2,4rD

1.1+2.2

0.006 -

0.000

< 183X

Can't measure

"Mg active ingredfents per ha based on free acid form."

. .. ; • EXAMPLE 6

Herbicidal Activity - , , - '

The effectiveness- of the formulations on- the control of various weeds in wheat is tested. The various
salts of the combination of dicamba-2,4-0 are applied at 0.06, 0.1 25 and 0.25 kg/ha dicamba and 6.38 kg/ha

' 25 ,2.4-d:.- . . ..... /. -..;/.; V . ■ ■ .

: Weeds evaluated include: . •
Amaranthus.retroflexus; (Pigweed)

Asclepias syriaca (Milkweed) , ,

Brassica campestris (Rape) '.
30 . Brassica kaber (Charlock) •' . .

Descurania.pinnata (Tansy mustard) • ••

Descurania sophia (Tansy mustard) .
Helianthus annus (Sunflower)
. Lactuca serriola (Wild lettuce) - *- ~.

35 ' ' '

Lamium amplexicaule (Henbit) •
. t Lapsana communis; (Nipplewort) ' - ■ ■*

Polygonum convolvulus (Climbing Buckwheat)
■ . Rumex crispus (Yellow dock) • •

. Salsola kali (Russian thistle) ' . ;' " \- .•

40 Thlaspi arvenge .(Field Penny-Cress) /.

- - : . ' All of the formulations, give substantially the same weed control as DMA formulations, showing, that the
various -salts- db 'not affect activity. Also amount of injury of the various salts is evaluated, and the various.

•salts -do- not affect the injury rate.' - ■ ■ *

45 , • " ' •

EXAMPLE 7 •

" 50 Following the protocol of Example 6, weed control and injury rate is evaluated in corn. Weeds which are
. evaluated include:
, Abutilon theophrasti (Velvet-leaf)
Amaranthus retroflexus (Pigweed) '
- Chenopodium album (Lamb's-quarters) .
55 Polygonum pensylvanicum (Pennsylvania smartweed) . r , * ' .

Solanum elaeagnifolium (Silverleaf. nightshade) '
Xanthium pensylvanicum' (Common cocklebur)

No significant differences are seen in either weed control or injury rate compared to DMA formulations.

' • ' 14 ' .

BNSCXDCID: <EP_0375624A1J_> „ -*'~ r -

EP 0 375 624 A1

EXAMPLE 8

. Following the protocol of Example 6, weed control and injury rate* is evaluated in sorghum. Weeds
5 which are evaluated include:

Amaranthus retroflexus (Redroot pigweed)

Ipomoea lacunosa (Pitted morningglory)

Polygonum pensylvanicum (Pennsylvania smartweed)

No significant differences are seen in either weed control or injury rate compared to DMA formulations. .

io ■ . ..

Claims

- 1. the amine salt of a /pesticidally active compound, wherein the amine is selected from the group
15 consisting of

■ a) Aminopropylmorpholine (APM) as shown by the Formula I

CH 2 -CH 2

/ N ■ •

„_0 • _ N-CH 2 -CH 2 -CH 2 -NH 2 \ . ._.„.!; . .. . . ... .

20 "■ • \ /

CH 2 -CH 2

b) Jeffamine D-230 as shown by the -formula II

H 2 N-CH-GH 2 -(0-CH 2 -CH-) n NH 2 II
CH 3 CH 3

30 wherein n is 2 or 3; .

c) Methyidiethanolamine (MDEA) as shown by the formula III

. CH3-N-(CH 2 -CH 2 -OH)2 Ml; , , '

d) 2-amino-2-ethyl-1 ,3-propanediol (AEPD) as shown by the formula IV

35 CH 2 -OH

H 2 N-C-CH 2 -CH 3 IV;
CH 2 -OH

40

e) Tris(hydroxymethyl)aminomethane"(Tris Amino) as shown by the formula V

CH 2 -0H
t

. H 2 N-C-CH 2 -OH V; and

CH 2 -OH

f) 2,4,6-Tris(dimethylaminomethyl)phenol (Actiron NX-3) and NaOH as shown by the formula VI

OH

50

55

(CH 3 ) 2 N-CH 2 ^^p

CH 2 -N(CH 3 ) 2 + Na0H . VIt

CH 3 -N(CH 3 ) 2

15

BNSOOCID: <EP_0375624A1JU>

EP 0 375 624 At

2. The salt.pf claim 1 having herbictdal activity. /
.3. The salt of claim 1 having fungicidal activity. - . , ; '

4. The salt of clsiim. 1 having insecticidal activity. ' —

5'. The salt of claim 1 wherein the pesticidally active compound is selected from the group consisting of
5 dicamba, 2,4-D, salts thereof, and mixtures thereof. ' '. •

6: The salt ofclaim 1 wherein the pesticidally active, compound is dicamba or a salt thereof.
■ 7. The salt'of claims 1-6 wherein the amine is APM. , •
' 8. A pesticidai composition" comprising the amine salt of claims 1-7 arid ah agriculturally acceptable

carrier. . . . ' - • . ■ -

/a ' , 9. A process, for .preparing the salt of claims 1-7 comprising combining a pesticidally active compound
with a salt-forming amine selected from the group consisting of.

' ' a) ^ as shown by .the Formula I — ••••••*-:• •: . ■ ^_ ~

' CH2-CH2

15 ■ . 0 ~ - ^N-CH 2 -CH 2 -CH 2 -NH2 . " I; . ■

"' CH 2 -CH 2 ' ...

'20

25.

30

35

40

b) Jeffamine 0-230 as shown by the formula II '

H 2 N-CH-CH 2 -(0-CH 2 -CH-) n NH 2 ' II

CH 3 : ; CH 3 - ■

wherein n is 2 or 3;. : .

c) Methyldiethanolamine (MDEA) as shown by the formula III • '
CH 3 -N-(CH2-CH 2 -OH) 2 . Ill; , '

: d> 2-amino-2-ethyl-1 1 3-propanediol (AEPD) as shown by the formula JV

CH 2 -0H

H 2 N-C-CH 2 -CH 3 . IV;
" - • ■' CH 2 -0H

3) Tris(hydroxymethyi)aminomethane (Tris Amino) as shown by the formula V

'' K : CH 2 -0H

. . . • . I ' . :

H 2 N-C-CH 2 -0H V; and

; CH2-0H

45

f) 2 ( 4 1 6-Tris(dimethylaminomethyl)phenol and NaOH (Actiron NX-3) and NaOH as shown by the
formula VI ' ' . . . .

-■. " • ; oh ^ * V; *

'so. (,CH3) 2 N-CH 2 « 7 ^v t -CH 2 -N<CH 3 ) 2 _ + NaOH VI.

•CH 3 -N(CH 3 ) 2 '

55

10. A method of combatting weeds comprising applying a herbicidally effective amount of the amine
salt of claims 2, 5 or 6 .to the weeds of their, locus.

16

BN8DOCID: <EP_0375624A1 JU>

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DOCUMENTS CONSIDERED TO BE RELEVANT

EP 89810966. .5

Category

Citation of document with indication, where appropriate,
of relevant passages

Relevant
to claim

CLASSIFICATION OF THE
APPLICATION tint CI s )

A '

DP - Al - 255 870
(AKADEMIE. DER LANDWIRTSCHAFTS-
WISSENSCHAFTEN)

* Abstract *

DP - Al - 255 869
(AKAPEMIE PER LANDWI RT S C HAF T S -
WISSENSCHAFTEN)

* Abstract *

PP - A3 - 161 202

( VEB CHEMIEKOMINAT 3ITTERFELP)

* Abstract *

1,8, 10

1,8, ic

1, 8, 1C

The present search report has been drawn up for all claims

A

01

N

25/18

A

01

N

33/02

A

01

N

33/04

A

01

■N

33/08

A

01

N

.4 3/84

TECHNICAL FIELDS
SEARCHED tint Cl s )

A. 01 N

Place of search
VIENNA

Date of completion of the search

21-02-1990

Examiner

2
e

CATEGORY OF CITED DOCUMENTS

X : particularly relevant if taken alone

Y : particularly relevant if combined with another

document of the same category
A : technological background
O : non-written disclosur
P : intermediate document '

T : theory or principle underlying the invention
E : earlier patent document, but published on, or

after th filing date
D : document cited in the application
L : document cited for other reasons

& : member of the same patent family, corresponding
document . . ■ .. ...

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I,

sr.-